Di-tert-butyl azodicarboxylate → HCID 46184202, compound

HRID 417077Notes

Reaction equation

HRID 417077 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:14][OH:15])[C:11]3[CH:22]=[C:23]([F:27])[C:24]([F:26])=[CH:25][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.O[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)[CH2:14][O:15][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)[C:11]3[CH:22]=[C:23]([F:27])[C:24]([F:26])=[CH:25][C:10]=3[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 97268Di-tert-butyl azodicarboxylateHCID 666193102-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanolHCID 178516071HCID 178516071, compound

Product 1

HCID 46184202HCID 46184202, compound

Procedure

The title compound was prepared in analogy to Example 4, intermediate, from 2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanol (Ex. 1, int. c) and 2-hydroxypyridine (commercially available) and replacing di-ethyl azodicarboxylate by di-tert-butyl azodicarboxylate. The crude product was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) with a gradient of n-heptane:ethyl acetate (100:0 to 50:50). White solid (79%). MS (Turbo Spray): m/z=468.3 [M+H].

Workup

  1. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-15f808335c6f46c5ad2b1a7f23a15565
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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